OFF MARKET

Off Market Jun 2025 for $312K

$340,972

Est. refi paymentEst. refi $2,138/mo

•

1,188

sq ft

104 Dutchess Rd, Chestertown, MD 21620

About this home

This home is a must see! Join the Chester Harbor Community. A charming home in a lovely neighborhood on Maryland's Eastern Shore. Welcome to Chester Harbor, Queen Anne's County. Only minutes from historic Chestertown, this three bedroom, two bath home offers one-level living and an appealing owner's suite. The expansive, fully fenced backyard is easily accessed from the private deck off of the kitchen. Extend your entertaining outside! Two sheds provide outside storage for your toys, and the patio is the perfect location to enjoy those Maryland Crabs. Roundtop Park is 20 acres of outdoor fun within the community. Located at the head of Rosin Creek, you can picnic, grill, play multiple sports and enjoy the playground as you get to know your neighbors or enjoy a family reunion at the pavilion. Storage is plentiful throughout and includes a large kitchen pantry. The wood-burning fireplace sets the tone for a cozy evening, and the multiple ceiling fans bring pleasure year round. Recent updates include a new AC unit in 2021, new bedroom carpets in 2022, a new furnace in 2023, as well as new flooring in the dining room and kitchen in 2024. Don't let this one slip by, schedule your appointment today!

Single-familyProperty Type

1989Year Built

0.34 acresLot Size

$287Est. Price/Sq.Ft.

4 spacesParking

Listed by Helen J Butler • Taylor Properties

•301-970-2447 (broker)

Bought with Brittany Fox • RE/MAX Chesapeake

•410-398-9200 (broker)

Redfin checked: 4 minutes ago

•Source:BRIGHT MLS #MDQA2013072

Redfin Estimate

$340,972

$29K since sold in June 2025$4,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3% higher than the average sale price ($331K) of 6 comparable homes.

SOLD MAR 31, 2026
$330,000
A
3 beds2 baths1,170 sq ft
129 Parma Rd, Chestertown, MD 21620
SOLD MAR 9, 2026
$317,000
B
3 beds2 baths1,232 sq ft
213 Central Dr, Chestertown, MD 21620
SOLD NOV 14, 2025
$322,000
C
3 beds2 baths1,232 sq ft
105 Parma Rd, Chestertown, MD 21620
SOLD MAR 18, 2026
$270,000
D
3 beds2 baths1,424 sq ft
119 Darden Rd, Chestertown, MD 21620
SOLD MAY 29, 2026
$430,000
E
3 beds2 baths1,588 sq ft
201 Birch Run Rd, Chestertown, MD 21620
SOLD AUG 14, 2026
$318,000
F
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620

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Earn from this home

Refinance

Est. cash available

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Rent

$2,465/mo

Redfin rental estimate

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Market trends in 21620, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.4%

+0.3% MoM

Median sale price

$355K

$7K MoM

Avg. days on market

48d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

$200,000
4 beds1 bath1,816 sq ft
223 Mount Vernon Ave, Chestertown, MD 21620
(443) 215-4663
NEW 20 HRS AGO
$329,900
2 beds2 baths1,440 sq ft
22974 Bay Shore Rd, Chestertown, MD 21620
(410) 822-6665
COMING SOON
$489,000
2 beds2 baths1,098 sq ft
105 N Water St #3, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$659,999
3 beds3 baths2,716 sq ft
7712 Waterview Ln, Chestertown, MD 21620
(410) 778-0330
$315,000
3 beds1 bath1,008 sq ft
24775 Langford Rd, Chestertown, MD 21620
(410) 398-9200
$289,000
3 beds2 baths1,056 sq ft
8732 Elm Rd, Chestertown, MD 21620
(410) 778-0330
$1,295,000
4 beds3.5 baths3,383 sq ft
8276 Broad Neck Rd, Chestertown, MD 21620
(410) 810-3900
$300,000
3 beds1 bath960 sq ft
104 Lincoln Dr, Chestertown, MD 21620
(443) 274-1900
COMING SOON
$568,900
4 beds2.5 baths2,464 sq ft
329 Union Church Rd, Chestertown, MD 21620
(443) 215-4663
$275,000
3 beds1 bath975 sq ft
7482 Poplar Ave, Chestertown, MD 21620
(301) 970-2447
See all

Provided by Redfin

Sale history for 104 Dutchess Rd

Date

Event

Price

BRIGHT MLS #MDQA2013072

Jun 20, 2025

Sold

$312,000

$263/sq ft

May 15, 2025

Contingent

—

Apr 24, 2025

Listed

$312,000

$263/sq ft

BRIGHT MLS #MDQA2001056

Nov 23, 2021

Sold

$245,000

$206/sq ft

Oct 9, 2021

Pending

—

Oct 1, 2021

Listed

$245,000

$206/sq ft

+27

Cute and Cozy Rancher! 3 Bedroom 2 Bathroom Home located in the Chester Harbor Community of Queen Anne's County Chestertown which boasts almost 1200 SQFT of Living Space - this listing is more than meets the eye with Wood Burning Fireplace, Oversized Rear BumpOut Addition, Fully Fenced in Back Yard on a Large Lot and matching Detached Shed. Wrap around Kitchen becomes your central hub as you can enjoy the front Family Room while serving snacks on the Bar Height Island or entertain with guests in the rear Formal Dining. Plus, take the good times outdoors through the Glass Slider onto your Private Back Deck! Interior as been freshly painted and offers Owners Suite with attached Full Bathroom so 2 additional Bedrooms can share a separate Full Hallway Bathroom. Low Maintenance Living and in a great location. Talkie or Atlantic Broadband Internet Available. Community is great for taking walks, riding bicycles, enjoying the neighborhood pier or picnic tables. Plus minutes from Historic Chestertown where you can enjoy the Farmers Market, Waterfront Dining, Boutiques, Fishing or Boating!!!

Public Records

Dec 17, 2007

Sold

$179,900

$151/sq ft

MRIS #QA6572132

Nov 21, 2007

Delisted

—

Oct 20, 2007

Listed

$151/sq ft

Public Records

Feb 25, 2003

Sold

$115,000

$97/sq ft

MRIS #QA4382775

Dec 31, 2002

Delisted

—

Dec 6, 2002

Listed

$101/sq ft

Public Records

Dec 6, 2002

Sold

$112,000

$94/sq ft

MRIS #QA4327828

Oct 3, 2002

Delisted

—

Sep 26, 2002

Listed

$96/sq ft

Public Records

Mar 30, 1999

Sold

$82,500

$69/sq ft

MRIS #QA2504578

Jan 27, 1999

Delisted

—

Jun 11, 1998

Listed

$75/sq ft

Public Records

Jan 28, 1991

Sold

$33,636

$28/sq ft

** Price available after signing in.

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Year

Property tax

Land + Additions

Assessment*

2025

$1,797 (+5.4%)

2024

$1,704 (+5.4%)

$76,000 + $158,800

$234,800

2023

$1,617 (+5.4%)

2022

$1,534 (+1.8%)

2021

$1,507 (+3.7%)

$56,000 + $100,500

$156,500

2020

$1,454 (+3.8%)

2019

$1,400 (+2.0%)

2018

$1,373 (+2.0%)

$56,000 + $83,700

$139,700

2017

$1,346 (+2.1%)

2016

$1,319

$47,200 + $84,100

$131,300

2015

$1,319 (−13.0%)

$47,200 + $84,100

$131,300

2014

$1,516

$82,100 + $69,700

$151,800

2013

$1,516 (+2.0%)

2012

$1,486 (−4.2%)

2011

$1,551 (+5.0%)

2010

$1,477 (+7.7%)

2009

$1,371

Tax history for 104 Dutchess Rd

Year

Property tax

Land + Additions

Assessment*

2025

$1,797 (+5.4%)

2024

$1,704 (+5.4%)

$76,000 + $158,800

$234,800

2023

$1,617 (+5.4%)

2022

$1,534 (+1.8%)

2021

$1,507 (+3.7%)

$56,000 + $100,500

$156,500

2020

$1,454 (+3.8%)

2019

$1,400 (+2.0%)

2018

$1,373 (+2.0%)

$56,000 + $83,700

$139,700

2017

$1,346 (+2.1%)

2016

$1,319

$47,200 + $84,100

$131,300

2015

$1,319 (−13.0%)

$47,200 + $84,100

$131,300

2014

$1,516

$82,100 + $69,700

$151,800

2013

$1,516 (+2.0%)

2012

$1,486 (−4.2%)

2011

$1,551 (+5.0%)

2010

$1,477 (+7.7%)

2009

$1,371

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.34 Acres

Year renovated

—

Sq. Ft.

1,188

Year built

1989

Style

Single Family Residential

County

Queen Anne's County

APN

02 003457

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

NC-20

Neighborhood Conservation-20 District

There are several varieties of NC Districts. The NC Districts are intended to preserve the character, density, and scale of existing residential neighborhoods. The NC Districts allow existing neighborhoods to conform to this Chapter 18:1, and they allow for in-fill development to be compatible with the surrounding area. NC Districts are designated for existing residential developments as follows: NC-20: 20,000 sq ft average lot size.; All NC District regulations apply to NC Districts with a T designation on the Zoning Maps; except that single-wide manufactured homes are a permitted use within NC-T Districts.

Permitted uses

Include but are not limited to:

Equestrian facility
Housing-Single unit
Housing-Multiple units
Public service
Recreation
Housing-Mobile home park

Property details

Parking

Parking Information
# of Total Garage and Parking Spaces: 4
Driveway - # of Spaces: 4
Driveway

Interior

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Appliances: Dishwasher, Dryer, Microwave, Oven/Range - Electric, Washer
Interior Features: CeilngFan(s), Dining Area, Entry Level Bedroom, Pantry
Living Area Sq.Ft. Source: Assessor

Room Information
Laundry Type: Has Laundry, Dryer In Unit, Washer In Unit

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Wood, Mantel(s), Screen

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $158,800
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Patio(s), Porch(es)
Roof: Architectural Shingle
Structure Type: Detached
Other Structures: Shed

Exterior Information
Fencing: Privacy, Rear, Wood

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $76,000

Above Grade Information
Finished Sq.Ft.: 1,188
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $1,966
Tax Assessed Value: $234,800
Tax Year: 2024
Tax Annual Amount: $1,966

Assessments Information
Year Assessed: 2025

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Propane - Leased
Hot Water: Propane
Sewer Septic: On Site Septic
Water Source: Well

Location

School Information
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: 50 East to 213 N Keep left onto S Commerce St, turn Right on Round Top Rd Turn left on Dutchess Rd, Destination is on your right
Road Responsibility: City/County

Waterfrontage Information
Water Oriented
Water Body Type: Creek
Water Body Name: Rosin Creek

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,188
Stories: 1.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1989
Year Renovated: —
County: Queen Anne's County
APN: 02 003457

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.0mi

5/10

Sudlersville Middle School

Public 5-8 • Assigned • 9.5mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 12.1mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 105° expected this year, 15 days in 30 years

6/10 Wind Factor

73% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Chestertown, MD • 21620

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.7 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$324,000 – $393,000

Sell confidently with a local market expert in Chestertown. 3 minutes to get started.

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COMING SOON

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3 beds2 baths1,056 sq ft

8732 Elm Rd, Chestertown, MD 21620

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4 beds3.5 baths3,383 sq ft

8276 Broad Neck Rd, Chestertown, MD 21620

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COMING SOON

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Home values near 104 Dutchess Rd

Data from public records.

Address	Redfin Estimate
210 Dutchess Road, Chestertown, MD - Beds \| 1 Baths \| 1080 Sq. Ft.	$289,455
202 Dutchess Road, Chestertown, MD 3 Beds \| 2 Baths \| 1508 Sq. Ft.	$323,513

Address	Redfin Estimate
206 Dutchess Road, Chestertown, MD - Beds \| 1.5 Baths \| 1464 Sq. Ft.	$286,027
103 Dutchess Road, Chestertown, MD 3 Beds \| 3 Baths \| 1248 Sq. Ft.	$396,874

Address	Redfin Estimate
205 Dutchess Road, Chestertown, MD 2 Beds \| 1.5 Baths \| 950 Sq. Ft.	$304,194
110 Dutchess Road, Chestertown, MD 2 Beds \| 1 Baths \| 1068 Sq. Ft.	$258,360

Property information provided by BRIGHT MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Sale history for 104 Dutchess Rd

Tax history for 104 Dutchess Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21620

Home values near 104 Dutchess Rd

More real estate resources